NP-MRD: Showing NP-Card for (5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0270184)

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Record Information

Version

2.0

Created at

2022-09-08 15:56:20 UTC

Updated at

2022-09-08 15:56:20 UTC

NP-MRD ID

NP0270184

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Fusicoccin P belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Diaporthe amygdali. Based on a literature review very few articles have been published on fusicoccin P.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082217562D          

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    0.7251    5.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0718    5.0868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    3.6524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4405    4.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    3.3367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7860    3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  3  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0270184

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@H]1CC[C@H]2[C@@H](C)[C@@H](O)[C@H](OC3O[C@H](CO)[C@@H](O)C(O)C3O)C3=C(C[C@H](O)[C@]3(C)C=C12)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O9/c1-12(2)16-8-19(29)27(4)9-17-14(11-34-5)6-7-15(17)13(3)21(30)25(20(16)27)36-26-24(33)23(32)22(31)18(10-28)35-26/h9,12-15,18-19,21-26,28-33H,6-8,10-11H2,1-5H3/t13-,14-,15+,18-,19+,21-,22-,23?,24?,25-,26?,27+/m1/s1

> <INCHI_KEY>
VOMYWCJIBGWNMX-AAIXAVPZSA-N

> <FORMULA>
C27H44O9

> <MOLECULAR_WEIGHT>
512.64

> <EXACT_MASS>
512.298532997

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.64972444478853

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6R)-2-{[(3R,4S,8R,9R,10R,11S,14S)-4,9-dihydroxy-14-(methoxymethyl)-3,10-dimethyl-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.24081942666666586

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.109345268910406

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.198384267269509

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083696312295

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
132.63560000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R)-2-{[(3R,4S,8R,9R,10R,11S,14S)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.177  -1.560   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.298  -0.025   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.028   0.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.149   2.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.462   3.187   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.103   4.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.568   4.806   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.978   3.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.556   2.794   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.133   3.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.374   1.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.543   4.806   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.008   4.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.008   5.856   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.506   5.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.522   7.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.649   3.187   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.962   2.383   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.083   0.848   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.133   6.228   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.044   7.317   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.442   8.805   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.930   9.204   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.328  10.691   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.816  11.090   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.905  10.001   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.240  11.780   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.638  13.268   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.752  11.381   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.663  12.470   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.353   9.894   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.134   9.495   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.556   6.818   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.556   8.358   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.978   6.228   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.067   7.317   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   10   19                                                  
CONECT   19   18                                                            
CONECT   20   12   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   20   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    7   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₉

Average Mass

512.6400 Da

Monoisotopic Mass

512.29853 Da

IUPAC Name

(5S,6R)-2-{[(3R,4S,8R,9R,10R,11S,14S)-4,9-dihydroxy-14-(methoxymethyl)-3,10-dimethyl-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(5S,6R)-2-{[(3R,4S,8R,9R,10R,11S,14S)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC[C@H]1CC[C@H]2[C@@H](C)[C@@H](O)[C@H](OC3O[C@H](CO)[C@@H](O)C(O)C3O)C3=C(C[C@H](O)[C@]3(C)C=C12)C(C)C

InChI Identifier

InChI=1S/C27H44O9/c1-12(2)16-8-19(29)27(4)9-17-14(11-34-5)6-7-15(17)13(3)21(30)25(20(16)27)36-26-24(33)23(32)22(31)18(10-28)35-26/h9,12-15,18-19,21-26,28-33H,6-8,10-11H2,1-5H3/t13-,14-,15+,18-,19+,21-,22-,23?,24?,25-,26?,27+/m1/s1

InChI Key

VOMYWCJIBGWNMX-AAIXAVPZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fusicoccum amygdali	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Fusicoccane diterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Polyol
Oxacycle
Acetal
Ether
Dialkyl ether
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.24	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.64 m³·mol⁻¹	ChemAxon
Polarizability	55.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586705

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0270184)

MOL for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0270184 ((5s,6r)-2-{[(3r,4s,8r,9r,10r,11s,14s)-4,9-dihydroxy-6-isopropyl-14-(methoxymethyl)-3,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-8-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)